The leading Republican presidential candidate appeared on the shock-jock's program more than two dozen times beginning in the late 1990s.

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Unearthed Trump interviews reveal his crude comments about his wife, other women

UNITED KINGDOM - JULY 01: An informal study of Prince CHARLES, the Prince of Wales, and Lady Diana SPENCER, whose wedding will take place at Saint-Paul's Cathedral, London on 29th July 1981. (Photo by Keystone-France/Gamma-Keystone via Getty Images)

Princess Diana wearing a tiara and diamond necklace on an official visit to Australia, April 12th 1983. (Photo by Tim Graham/Getty Images)

LONDON - JULY 29: (FILE PHOTO) Prince Charles, Prince of Wales and Diana, Princess of Wales leave St. Paul's Cathedral following their wedding July 29, 1981 in London, England. (Photo by Anwar Hussein/Getty Images)

LONDON - JULY 29: Diana, Princess of Wales and Prince Charles ride in a carriage after their wedding at St. Paul's Cathedral July 29, 1981 in London, England. (Photo by Anwar Hussein/WireImage)

Prince Charles and Diana, Princess of Wales (1961 - 1997) pose together during their honeymoon in Balmoral, Scotland, 19th August 1981. (Photo by Serge Lemoine/Getty Images)

Princess Diana wearing a Jasper Conran suit during a visit to a community centre in Brixton, October 1983. (Photo by Princess Diana Archive/Getty Images)

PARIS, FRANCE: Britain's Princess Diana arrived in Paris Friday, 13 November, 1992, on a private three day visit she is making without her husband, Prince Charles. (Photo credit should read JOEL ROBINE/AFP/Getty Images)

The Princess of Wales visits Chinatown in Liverpool, April 1982. She is pregnant with Prince William, and wearing a pink wool maternity coat by Bellville Sassoon and a hat by John Boyd. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)

WINDSOR, UNITED KINGDOM - JUNE 06: Princess Diana At Polo, Just Two Weeks Before The Birth Of Her First Child, Prince William. Wearing A Maternity Dress Designed By Fashion Designer Catherine Walker She Is Walking With Sarah Ferguson. (Photo by Tim Graham/Getty Images)

LONDON - JUNE 22: New born Prince William with Diana, Princess of Wales and Prince Charles leave St. Mary's hospital on June 22, 1982 in Paddington, London, England,. He was born in the Lindo Wing of the hospital on June 21. (Photo by David Levenson/Getty Images)

NEW ZEALAND - APRIL 18: Princess Diana And Prince William In New Zealand. (Photo by Tim Graham/Getty Images)

(FILES) This picture taken 17 June 1997 shows Diana, Princess of Wales, a key volunteer of the British Red Cross Landmine Campaign at Red Cross headquarters in Washington DC. Princess Diana may have survived her fatal Paris car crash in 1997 if French medical staff had not wasted precious time, a leading British surgeon indicated at her inquest 19 November 2007. AFP PHOTO/FILES/Jamal (Photo credit should read JAMAL A. WILSON/AFP/Getty Images)

The Prince and Princess of Wales visit Barmouth in Wales, November 1982. She wears a suede beret by John Boyd and a coatdress by Arabella Pollen. (Photo by Terry Fincher/Princess Diana Archive/Getty Images)

The Princess of Wales visits University College Hospital in London, December 1982. She wears a John Boyd hat and a velvet suit by Caroline Charles. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)

LONDON, UNITED KINGDOM - FEBRUARY 01: Princess Diana And Prince Charles With Prince William And His Koala Bear Toy At Kensington Palace (Photo by Tim Graham/Getty Images)

Princess Diana (1961 - 1997) at the School of the Air, in Alice Springs, Australia, 30th March 1983. She is wearing a dress by Jan van Velden. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)

AYERS ROCK, AUSTRALIA - MARCH 21: Prince Charles, The Prince Of Wales And Diana, Princess Of Wales Standing In Front Of Ayers Rock During Their Official Tour Of Australia (Photo by Tim Graham/Getty Images)

NEW ZEALAND - APRIL 18: Princess Diana During A Visit To New Zealand Wearing A Dress Designed By Fashion Designer Donald Campbell (Photo by Tim Graham/Getty Images)

MANUKAU - APRIL 19: Diana Princess of Wales meets firemen during a visit to Manukau, near Auckland, New Zealand during the Royal Tour of New Zealand on April 19, 1983. Princess Diana wore a suit designed by Jan Van Velden, with a hat by John Boyd. (Photo by David Levenson/Getty Images)

CANADA - JUNE 23: Princess Diana in Edmonton during an official visit of Canada (Photo by Tim Graham/Getty Images)

VENICE, ITALY - MAY 5: (FILE PHOTO) (L-R) Diana the Princess of Wales holds her son Harry, whilst looking at Prince William held by his father Prince Charles on May 5, 1985 in Venice, Italy. Prince William will celebrate his 21st birthday on June 21, 2003. (Photo by Georges de Keerle/Getty Images)

LA SPEZIA, ITALY - APRIL 20: The Prince and Princess of Wales in La Spezia during a tour of Italy. (Photo by Tim Graham/Getty Images)

TWERTON ON AVON - MAY 31: Diana Princess of Wales meets girl guides outside the Poolemead centre for the Deaf on May 31, 1985 in Twerton on Avon, Bath, Avon. (Photo by David Levenson/Getty Images)

Princess Diana (1961 - 1997) inspects a guard of honour during a two-day visit to the 1st Battalion, the Royal Hampshire Regiment in Berlin, October 1985. She is wearing a pink and black suit by Victor Edelstein and a hat by Frederick Fox. (Photo by Lucy Levenson/Princess Diana Archive/Getty Images)

UNITED KINGDOM - OCTOBER 04: Diana, Princess of Wales with her sons, Prince William and Prince Harry, at the piano in Kensington Palace (Photo by Tim Graham/Getty Images)

KLOSTERS, SWITZERLAND - FEBRUARY 06: Prince Charles With Princess Diana On A Ski-ing Holiday Together. The Princess Is Wearing A Red 'head' Ski Suit And A Headband And She Is Holding A Pair Of 'dynamic' Skis. The Prince Is Wearing A Blue Ski Suit And Carrying A Pair Of 'k2' Skis. (Photo by Tim Graham/Getty Images)

VIENNA - APRIL 16: Diana, Princess of Wales, wearing a sapphire diamond and pearl necklace, attends a banquet on April 16, 1986 in Vienna, Austria (Photo by Anwar Hussein/Getty Images)

UNITED KINGDOM - AUGUST 22: PRINCESS DIANA ON BOARD HMS TRAFALGAR NUCLEAR SUBMARINE MEETING THE CREW DURING A VISIT TO THE NAVAL SUBMARINE BASE IN FASLANE IN THE FIRTH OF CLYDE, SCOTLAND (Photo by Tim Graham/Getty Images)

SANDHURST - APRIL 10: Diana, Princess of Wales wears a Catherine Walker white suit with drum majorette gold frogging and epaulettes and a graham smith hat for her visit to the Sandhurst Military Academy on April 10, 1987 in Sandhurst, England (Photo by Anwar Hussein/Getty Images)

CHAMBORD, FRANCE - NOVEMBER 09: Diana, Princess of Wales, wearing a white and blue lace and sequin evening coat-dress designed by Catherine Walker for a dinner at the Chateau de Chambord during her official visit to France. (Photo by Tim Graham/Getty Images)

The Princess of Wales at the museum in Kuwait City, March 1989. She is wearing a gold embroidered bedouin gown that was presented to her with a silver tea set to mark the occasion of her visit. (Photo by Jayne Fincher/Getty Images)

The Princess of Wales with her sons William and Harry on the chair lift during a skiing holiday in Lech, Austria, April 1991. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)

LONDON, ENGLAND - MARCH 7 Diana, Princess of Wales attends the Premiere of Dangerous Liaisons, in London's West End, on March 7, 1989 in London, United Kingdom. (Photo by Julian Parker/UK Press via Getty Images)

ABU DHABI, UNITED ARAB EMIRATES - MARCH 15: The Prince And Princess Of Wales attend a desert picnic on March 15, 1989 in Adu Dhab, United Arab Emirates. (Photo by Georges De Keerle/Getty Images)

LONDON, UNITED KINGDOM - SEPTEMBER 11: Princess Diana With Her Sons Prince William And Prince Harry Standing On The Steps Of Wetherby School On The First Day For Prince Harry. (Photo by Tim Graham/Getty Images)

INDONESIA - NOVEMBER 05: The Princess Of Wales Playing Bowls At Sitanalia Leprosy Hospital In Indonesia (Photo by Tim Graham/Getty Images)

NIGERIA - JUNE 3: (FILE PHOTO) (PRINCESS DIANA RETROSPECTIVE 17 OF 22) The Princess of Wales speaks with Nigerians circa 1990 during a visit to Nigeria. Princess Diana, 36-years-old, died with her companion Dodi Fayed, 41-years-old, in a car crash August 31, 1997 in Paris, France. Fayed was the son of an Egyptian billionaire. (Photo by Georges De Keerle/Getty Images)

The Princess of Wales and the Queen Mother in an open-topped landau on their way to the Royal Ascot race meeting, June 1990. The Princess wears a Catherine Walker suit and a Philip Somerville hat. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)

The Princess of Wales walks amongst crowds of children waving flags during her visit to Cullompton in Devon, September 1990. She is wearing a Catherine Walker dress. (Photo by Terry Fincher/Princess Diana Archive/Getty Images)

WASHINGTON, UNITED STATES - OCTOBER 05: Princess Diana With Mrs Barbara Bush At The White House (Photo by TIM GRAHAM/Getty Images)

Diana, The Princess Of Wales Takes Her Sons, Prince'S William, And Harry Out On The Boat ' Maid Of The Mist ' To View Niagara Falls. (Photo by Julian Parker/UK Press via Getty Images)

LONDON, UNITED KINGDOM - NOVEMBER 18: Diana Princess of Wales attends the Premiere of Hot Shots, in London's West End, on November 18, 1991 in London, United Kingdom. (Photo by Julian Parker/UK Press via Getty Images)

The Princess of Wales (1961 - 1997) talks to children at the British school in Seoul during a visit to Korea, 1992. (Photo by Linda Grove/Getty Images)

INDIA - FEBRUARY 11: Diana Princess of Wales sits in front of the Taj Mahal during a visit to India (Photo by Tim Graham/Getty Images)

CALCUTTA;INDIA - FEBRUARY: Princess Diana the Princess of Wales holds hands with a nun at Mother Teresa's Hospice in Calcutta during her visit to India in February of 1992. (Photo by Anwar Hussein/Getty Images)

GIZA, EGYPT - MAY 12: Diana Princess of Wales visiting the Pyramids in Giza during an official tour of Egypt. (Photo by Tim Graham/Getty Images)

Princess Diana (1961 - 1997) during a visit to the Red Cross borehole project for refugees in Zimbabwe, July 1993. She is wearing a safari suit by Catherine Walker. (Photo by Jayne Fincher/Getty Images)

Princess Diana (1961 - 1997), Prince Harry, Prince William and Prince Charles at a parade in the Mall, London, during V.J. Day commemorations, August 1994. Diana is wearing a Tomasz Starzewski suit and a hat by Philip Somerville. (Photo by Terry Fincher/Getty Images)

UNITED KINGDOM - MAY 20: Princess Diana Reviewing The Troops Of The Princess Of Wales Regiment In Kent. The Princess Is Wearing A Pink Suit Designed By Versace. (Photo by Tim Graham/Getty Images)

LONDON -OCTOBER 08: Diana, Princess of Wales laughs as she visits the London Lighthouse, the HIV/Aids charity, to help launch it's Â£1.5 million Capital Appeal on October 08, 1996 in London, England . (Photo by Anwar Hussein/Getty Images)

WINDSOR, UNITED KINGDOM - MARCH 09: Official Portrait Of The Royal Family On The Day Of Prince William's Confirmation. Front Left To Right - Prince William, Princess Diana, Prince William, Prince Charles And The Queen. Back Left To Right - King Constantine, Lady Susan Hussey, Princess Alexandra, Duchess Of Westminster And Lord Romsey (Photo by Tim Graham Picture Library/Getty Images)

GREAT BRITAIN - JUNE 06: Diana, Princess of Wales crouching down to embrace a pupil at the Shri Swaminarayan Mandir in Neasden (Photo by Tim Graham/Getty Images)

Diana, The Princess Of Wales Visits Washington, Usa.Gala Dinner Held By The American Red Cross, To Raise Funds For Landmine Victims Around The World. . (Photo by Mark Cuthbert/UK Press via Getty Images)

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Trump's remarks mostly focused on sex and his opinions about what constituted a great woman - which mostly concerned breast size.

"A person who is very flat-chested is very hard to be a 10," Trump told Stern. He also said he found Angelina Jolie unattractive because her lips were too big.

He spoke often of Princess Diana, saying he could have bedded her.

"She had the height, she had the beauty, she had the skin. She was crazy, but these are minor details."

In an exchange about Pamela Anderson's hepatitis C diagnosis in 2000, Stern asks Trump "Would you do her, still?"

In 1997, after buying the Miss USA pageant, Trump boasted that his goal was to make the "bathing suits to be smaller and the heels to be higher."

Eight years later, while promoting the contest on Stern's show, Trump advised, "If you're looking for a rocket scientist, don't tune in tonight, but if you're looking for a really beautiful woman, you should watch."

In another interview, Trump said he wanted to have children with his new wife, Melania. But he wouldn't spend any time with them, he said.

"'Cause I like kids. I mean, I won't do anything to take care of them. I'll supply funds and she'll take care of the kids. It's not like I'm gonna be walking the kids down Central Park," he told Stern.